1. Field of the Invention
The present invention relates to a process for producing optically active and physiologically active compounds, particularly optically active compounds having high optical purity useful as starting materials for tomoxetine, fluoxetine and the like, namely optically active 1-phenyl-1,3-propanediols.
2. Description of the Prior Art
Tomoxetine and fluoxetine that are useful as antidepressants have two kinds of optical isomers because they have an asymmetric carbon atom. In the isomers, S-compounds alone have effect as antidepressants. For practical purposes, it is necessary to use the S-compounds alone, because the racemates or compounds having low optical purity do not show sufficient physiological activity (Drugs Future, 11, 134(1986), S. I. Ankier, Prog. Med. Chem., 23, 121(1986)).
When optically active tomoxetine or fluoxetine is produced, optically active 1-phenyl-1,3-propanediol is usefull, as a starting material. However, there is little literature of methods for obtaining optically active 1-phenyl-1,3-propanediol having high optical purity, so that it is long-awaited to find a simple purification method for easily improving the optical purity (Y. Gao and K. B. Sharpless, J. Org. Chem., 53, 4081(1988)).
Furthermore, though physiological activity of analogues of tomoxetine or fluoxetine having a substituted group on the phenyl group has not been studied, revelation of higher physiological activity is expected by the effect of the substituted group.
The present invention provides a simple purification method for easily improving optical purity to efficiently obtain optically active 1-phenyl-1,3-propanediols having high optical purity.